stavudine-5'-α-naphthyl O-methoxy-L-alanyl phosphate | 905601-31-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: stavudine-5'-α-naphthyl O-methoxy-L-alanyl phosphate
• 英文别名: methyl (2S)-2-[[[(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy-naphthalen-1-yloxyphosphoryl]amino]propanoate
• CAS: 905601-31-2
• 化学式: C₂₄H₂₆N₃O₈P
• 分子量: 515.46
• InChiKey: KUPUOQIRQZUZBN-GBIQUIERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  stavudine-5'-α-naphthyl O-methoxy-L-alanyl phosphate 在 lipase 作用下， 以 甲醇 、 水 为溶剂， 生成 萘酚 、 司他夫定
  参考文献：
  名称：

  Synthesis and metabolism of naphthyl substituted phosphoramidate derivatives of stavudine

  摘要：

  The synthesis of naphthylphosphoramidate derivatives of stavudine was achieved using a four-step procedure. The derivatives were subjected to several different enzymes including lipase, esterase, Subtilisin Carlsberg, and Carica papaya, and their hydrolysis rates were determined. Based on the rates of hydrolysis, we were able to differentiate between the chiralities at the phosphorus center of the phosphoramidate compounds. In addition, lipase was found to distinguish between both alpha and beta forms of the compounds. The superior chiral selectivity shown by lipase toward the naphthyl substituted phosphoramidate derivatives is attributed to the restrictive binding pocket of the lipase. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.006
• 作为产物：
  描述：

  1-萘基二氯磷酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 生成 stavudine-5'-α-naphthyl O-methoxy-L-alanyl phosphate
  参考文献：
  名称：

  Synthesis and metabolism of naphthyl substituted phosphoramidate derivatives of stavudine

  摘要：

  The synthesis of naphthylphosphoramidate derivatives of stavudine was achieved using a four-step procedure. The derivatives were subjected to several different enzymes including lipase, esterase, Subtilisin Carlsberg, and Carica papaya, and their hydrolysis rates were determined. Based on the rates of hydrolysis, we were able to differentiate between the chiralities at the phosphorus center of the phosphoramidate compounds. In addition, lipase was found to distinguish between both alpha and beta forms of the compounds. The superior chiral selectivity shown by lipase toward the naphthyl substituted phosphoramidate derivatives is attributed to the restrictive binding pocket of the lipase. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.04.006

文献信息

• Synthesis and metabolism of naphthyl substituted phosphoramidate derivatives of stavudine
  作者：T.K. Venkatachalam、S. Qazi、F.M. Uckun

  DOI：10.1016/j.bmc.2006.04.006

  日期：2006.8

  The synthesis of naphthylphosphoramidate derivatives of stavudine was achieved using a four-step procedure. The derivatives were subjected to several different enzymes including lipase, esterase, Subtilisin Carlsberg, and Carica papaya, and their hydrolysis rates were determined. Based on the rates of hydrolysis, we were able to differentiate between the chiralities at the phosphorus center of the phosphoramidate compounds. In addition, lipase was found to distinguish between both alpha and beta forms of the compounds. The superior chiral selectivity shown by lipase toward the naphthyl substituted phosphoramidate derivatives is attributed to the restrictive binding pocket of the lipase. (c) 2006 Elsevier Ltd. All rights reserved.